Sorry for the delay! I was able to fix the issue. Your hunch was correct. I had to unpair and repair my Apple Watch with my phone and it is now fixed. Thanks!

Hi John Copses, you've been having this issue since the beginning right? We're still investigating why your iCloud sync doesn't work. We haven't been able to reproduce yet and this is the only case we've heard of so far, so I'm wondering if there's something wrong with your Apple Watch setup.